Kentucky Derby Hats: The Most Memorable Celebrity Headwear!

Dizziness: The Kentucky Derby is back!

The event, which takes place at the Churchill Downs racetrack in Louisville, Kentucky, has a star-studded history filled with over-the-top style. However, amid the coronavirus pandemic, 2020 race plans have been postponed due to health concerns. Instead of the traditional three charity galas and a red carpet for Hollywood’s biggest stars, racing fans had to watch the jockey riders from a safe distance when the race returns in May 2021.

Over the years the Derby has been filled with darling dresses and stunning styles that always give us our dose of fabulous fashion!

There were certainly some pretty floral dresses and gorgeous costumes worn for the event, but the Kentucky Derby is really all about the accessories. With that in mind, we decided to take a trip down memory lane and look back at the best, craziest, and most absurd headwear stars have worn.

From Nicole Richie And Gabrielle Union to Queen Elizabeth II herself, A-listers always show up on the runway with jaw-dropping and awe-inspiring hairstyles.

In 2004, Jessica Simpson attended with her then husband Nick Lachey and she went big for the occasion — literally! The reality star paired her cute floral sundress with a huge candy pink hat.

Five years later, Kim Kardashian participated in the Kentucky Derby. She kept her outfit simple, but served up a bit of glamor with an abstract gray hat that has since made fashion history.

When the 2013 race took place, Lauren Conrad stole the show, rocking a monochromatic ensemble. She paired her cute polka dot dress with a linen and tulle head covering that looked girly and feminine.

Kendra Wilkinson was another standout, taking a detour to traditional floral and brightly colored sundresses. Instead, she opted for a sleek white blouse and black pants. As for his headgear? She donned a wide-brimmed hat adorned with feathers.

But not all stars opt for a simple or traditional helmet. Some take risks with their Kentucky Derby accessories.

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For example, in 2015, Sarah Hyland paired her floral-print midi dress with a burgundy fascinator that was nothing if not unique. The mattress topper featured a red mesh, a velvet flower and a few bird feathers.

Another savage? michelle williams‘ blush and blue over-the-top, which had large tulle and lace details, at the 2019 Kentucky Derby.

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From Jessica Simpson in 2004 to Giada De Laurentiis in 2017 and everyone in between, keep scrolling to check out the most memorable Kentucky Derby headdresses: